tert-Butyl 3-(4-(tert-Butoxycarbonylamino)-1H-indol-1-yl)-3-(4-chlorophenyl)pent-4-ynoate → tert-Butyl 3-(4-(tert-butoxycarbonylamino)-1H-indol-1-yl)-3-(4-chlorophenyl)pentanoate

HRID 1427290Notes

Reaction equation

HRID 1427290 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[C:18]([C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)([C:27]#[CH:28])[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.O=[Pt]=O>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[C:18]([C:29]1[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=1)([CH2:27][CH3:28])[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 86705058tert-Butyl 3-(4-(tert-Butoxycarbonylamino)-1H-indol-1-yl)-3-(4-chlorophenyl)pent-4-ynoate

Product 1

HCID 117809455tert-Butyl 3-(4-(tert-butoxycarbonylamino)-1H-indol-1-yl)-3-(4-chlorophenyl)pentanoate

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To a solution of the product of Step E (150 mg, 0.3 mmol) in ethanol (3 mL) was added PtO2 (6.8 mg, 0.03 mmol) at room temperature under H2 atmosphere for 2 h. The solid was filtered off and the filtrate was concentrated in vacuo to give the title compound as colorless oil. LC/MS m/z=499.2[M+H]+.

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e93cc07712a246a2a74519912ce12465
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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